METHYL 4-BROMOCROTONATE

Product Name: METHYL 4-BROMOCROTONATE
CAS No.: 6000-00-6
Chemical Name: METHYL 4-BROMOCROTONATE
Synonyms: methyl (E)-4-bromobut-2-enoate;(E)-Methyl 4-bromocrotonate;Methyl (E)-4-bromo-2-butenoate;Neratinib Impurity 37;TRANS-METHYL-4-BROMOCROTONATE;Methyl (2E)-4-bromobut-2-enoate;METHYL TRANS-4-BROMO-2-BUTENOATE;Methyl trans-4-bromocrotonate 97%;4-BROMOCROTONIC ACID METHYL ESTER;trans-Methyl-4-bromocrotonate, 97 %
CBNumber: CB4109035
Molecular Formula: C5H7BrO2
Formula Weight: 179.01
MOL File: 6000-00-6.mol

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METHYL 4-BROMOCROTONATE Property

Melting point:: 83-85℃
Boiling point:: 83-85 °C13 mm Hg(lit.)
Density: 1.522 g/mL at 25 °C(lit.)
refractive index: n20/D 1.501
Flash point:: 197 °F
storage temp.: 2-8°C
solubility: Chloroform (Slightly), Methanol (Slightly)
form: Oil
color: Colourless
BRN: 1745755
InChI: InChI=1S/C5H7BrO2/c1-8-5(7)3-2-4-6/h2-3H,4H2,1H3/b3-2+
InChIKey: RWIKCBHOVNDESJ-NSCUHMNNSA-N
SMILES: C(OC)(=O)/C=C/CBr
CAS DataBase Reference: 6000-00-6(CAS DataBase Reference)

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Safety

Hazard Codes: Xi
Risk Statements: 37/38-41-36/37/38
Safety Statements: 26-39
WGK Germany: 3
RTECS: GQ3120000
F: 8-9
HS Code: 29161900
Storage Class: 10 - Combustible liquids
Hazard Classifications: Eye Irrit. 2
Skin Irrit. 2
STOT SE 3

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 16505
Product name: Methyl trans-4-bromo-2-butenoate
Purity: technical, ≥90% (GC)
Packaging: 5ml
Price: $155
Updated: 2026/03/19

Sigma-Aldrich

Product number: 16505
Product name: Methyl trans-4-bromo-2-butenoate
Purity: technical, ≥90% (GC)
Packaging: 25ml
Price: $469
Updated: 2026/03/19

TRC

Product number: M294005
Product name: Methyltrans-4-Bromo-2-butenoate(>85%)
Packaging: 25g
Price: $450
Updated: 2021/12/16

Matrix Scientific

Product number: 096464
Product name: (E)-Methyl 4-bromobut-2-enoate
Purity: 90%
Packaging: 5g
Price: $65
Updated: 2021/12/16

Matrix Scientific

Product number: 096464
Product name: (E)-Methyl 4-bromobut-2-enoate
Purity: 90%
Packaging: 25g
Price: $185
Updated: 2021/12/16

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METHYL 4-BROMOCROTONATE Chemical Properties,Usage,Production

Chemical Properties

light yellow liquid

Uses

Methyl trans-4-Bromo-2-butenoate is used as a reagent in the synthesis of several organic compounds including that of dimethoxy ketals and ketones via electrochemical oxidative decarboxylation of malonic acids.

Uses

Methyl trans-4-bromo-2-butenoate (Methyl 4-bromocrotonate) was used in the synthesis of highly substituted benzoxepines or benzopyrans and L-α-amino [4,5-³H]adipic acid.

Synthesis

67-56-1

13991-36-1

1117-71-1

The general procedure for the synthesis of methyl 4-bromobut-2-enoate from methanol and (E)-4-bromobut-2-enoic acid was as follows: (E)-4-bromobut-2-enoic acid (1.525 g, 9.24 mmol) and anhydrous methanol (10 ml) were added into a 50 ml three-necked flask, and stirred at 0 °C until complete dissolution. Thionyl chloride (5.49 g, 46.19 mmol, 5 ml) was added slowly dropwise, and bubbles were observed during the dropwise addition. After the dropwise addition, the reaction mixture was gradually warmed up to room temperature and stirring was continued for 15 h. The completion of the reaction was monitored by thin layer chromatography (TLC). After completion of the reaction, the solvent was evaporated to dryness under reduced pressure and the residue was extracted with ethyl acetate and water. The organic phase was separated and dried with anhydrous sodium sulfate. The dried organic phase was concentrated by rotary evaporator to obtain the crude product. The crude product was purified by column chromatography with the eluent ratio of petroleum ether:ethyl acetate=8:1, and the final product was methyl 4-bromobut-2-enoate (1.54 g, 93.1% yield) as a red oily liquid.

References

[1] Patent: CN107556289, 2018, A. Location in patent: Paragraph 0112; 0117; 0118; 0119
[2] Tetrahedron Asymmetry, 2009, vol. 20, # 10, p. 1164 - 1167

METHYL 4-BROMOCROTONATE Preparation Products And Raw materials

Raw materials

Preparation Products

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METHYL 4-BROMOCROTONATE Suppliers

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View Lastest Price from METHYL 4-BROMOCROTONATE manufacturers

Career Henan Chemical Co

Product: METHYL 4-BROMOCROTONATE 6000-00-6
Price: US $1.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: Customized
Release date: 2019-05-25

6000-00-6, METHYL 4-BROMOCROTONATERelated Search:

Oleic acid Methacrylic acid Methyl 4-bromocrotonate 4-BROMOCROTONIC ACID

(E)-4-Bromo-but-2-enoicacidmethylester

TRANS-METHYL 4-BROMO-2-BUTENOATE, STAB.

trans-Methyl-4-bromocrotonate, 97 %

Methyl trans-4-bromocrotonate 97%

Methyl (2E)-4-bromobut-2-enoate

(2E)-4-Bromo-2-butenoic acid methyl ester

(E)-4-Bromo-crotonic acid methyl ester

(E)-Methyl 4-bromocrotonate

(2E)-2-Butenoic acid, 4-broMo-, Methyl ester

Methyl trans-4-broMo-2-butenoate technical, >=90% (GC)

(E)-4-Bromo-2-butenoic acid methyl ester

Methyl (E)-4-bromo-2-butenoate

Methyl <I>trans</I>-4-bromo-2-butenoate

2-Butenoic acid, 4-bromo-, methyl ester, (2E)-

4-BROMOCROTONIC ACID METHYL ESTER

METHYL TRANS-4-BROMO-2-BUTENOATE

TRANS-4-BROMO-2-BUTENOIC ACID METHYL ESTER

TRANS-METHYL-4-BROMOCROTONATE

methyl (E)-4-bromobut-2-enoate

Methyl trans-4-Bromo-2-butenoate (>85%)

Neratinib Impurity 37

(E)-Methyl 4-bromobut-2-enoate (Afatinib Impurity)

6000-00-6

1117-71-7

BrCH2CHCHCOOCH3

HALOGEN

Organic Building Blocks

Building Blocks

Carbonyl Compounds

C2 to C5

Esters